Contentful
Large (~1,000)
Tailscale
Small (~290)
Best For
Contentful
Best for: Backend and full-stack engineers who want to work on developer-facing content infrastructure with remote flexibility and an established product used by major brands
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
ContentfulTailscale
3.4
4.4
Overall
3.8
4.5
Work-Life Balance
3.5
4.5
Culture & Values
3.4
4.4
Comp & Benefits
3.2
4.2
Senior Mgmt
3.2
4.2
Career Opps
👍 68% Recommend
👤 71% CEO Approval (Jaspar Carmichael-Jack)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Contentful only
🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Shared
🌐 Remote-Friendly⚙️ Engineering-Driven
Pros & Cons
Contentful
- Flexible remote/hybrid setup with strong distributed team culture
- Talented and humble engineering team with approachable, responsive leadership
- Stagnating product development with competition overtaking in key areas
- Internal promotions are difficult with pay disparities between long-tenured and new hires
Tailscale
- Same pay worldwide with 26 weeks parental leave and genuine work-life balance
- Brilliant, nerdy CEO who deeply understands the tech — culture is intellectual and respectful
- Career progression limited — only 3.0/5 on career opportunities
- Middle management still developing — some growing pains as the org scales
Bottom Line
Contentful
Pioneer in headless CMS with genuine remote flexibility, but Glassdoor is below average (3.4, 68% recommend) — reviews mention leadership instability and limited career progression.
Tailscale
Intellectual, engineer-led culture with same pay worldwide and 26 weeks parental leave — but career progression is limited and middle management is still maturing.
Open Roles
Contentful — 114 jobs
💻 Engineering
56
📋 Product
17
💼 Sales / GTM
13
📊 Data
6
📣 Marketing
4
🧠 ML / AI
2
⚖️ Legal
1
🎧 Support
1
Tailscale — 53 jobs
💻 Engineering
25
💼 Sales / GTM
12
📋 Product
6
⚙️ Operations
4
📊 Data
2
📣 Marketing
2
Summary
Contentful scores 3.4/5.0 on Glassdoor with a 3.8 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 1.0-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Engineering-Driven. Contentful also emphasizes Learning & Growth, Direct Product Impact. Tailscale also emphasizes Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent.
On the hiring front, Contentful has 114 open roles and Tailscale has 53 open roles.